After arriving in the US with $500, former tennis player Andres Bernal began investing in Connecticut real estate in 2016; a decade later, he says he owns more than 60 rental units worth over $12 million

Bernal’s approach has also evolved with the performance of individual properties. He and his partners have sold some older Connecticut properties where substantial equity was tied up but cash flow no longer justified holding them.

When Andres Bernal arrived in the United States with $500, his immediate goal was not to build a real estate empire. The Dominican-born former professional tennis player had come to pursue the sport he had played since childhood. But after years of teaching tennis and working long hours, he began looking for a different route to financial independence.Real estate, a concept he had first encountered through his family in the Dominican Republic, eventually became that route. His first investment came in 2016. Nearly a decade later, Bernal says his Connecticut portfolio has grown to more than 60 rental units valued at over $12 million, states a podcast interview published by Harbordise Partners.

From tennis courts to property seals

Bernal’s introduction to real estate began long before his first investment. His godfather was a builder in the Dominican Republic, and Bernal had watched him acquire and develop property while growing up.After playing professional tennis for nearly two years in the US, Bernal began teaching the sport, sometimes working 50 to 60 hours a week. Looking for a way to build income beyond trading time for money, he started studying stocks, businesses and real estate, states the interview. He eventually focused on property investing, learning the fundamentals before making his first investment in 2016.The strategy has since expanded beyond long-term rentals. Bernal completed more than 50 property flips during 2024 and 2025, building a business around acquisitions, renovations and sales while continuing to grow his rental portfolio.

A portfolio built around different tenants

According to the video interview, his Connecticut holdings include multifamily properties, duplexes, single-family homes and student rentals. Some properties operate through the federal Section 8 housing program, while others serve traditional tenants. Student housing has become an important part of the portfolio. Bernal owns properties near three Connecticut universities and typically rents homes to groups of students whose parents or family members co-sign their leases. Keeping properties within walking distance of campuses is another central part of the strategy, reducing the need for parking and transportation.His Section 8 properties provide another source of rental income, although they come with additional inspections and administrative requirements. Bernal says he has about 22 units connected to the program.

Building the business behind the properties

Managing dozens of properties and completing frequent flips requires more than finding deals. Bernal has built a network of contractors and property-management support to keep the operation moving. His flipping operation includes about a dozen contractors handling work such as carpentry, painting and basic plumbing and electrical tasks. A smaller part-time team manages the rental portfolio. That structure allows the same network of workers to move between renovation projects and maintenance needs, reducing the need to constantly find new contractors.

Knowing when to hold and when to sell

Bernal’s approach has also evolved with the performance of individual properties. He and his partners have sold some older Connecticut properties where substantial equity was tied up but cash flow no longer justified holding them. His renovation philosophy follows a similar hierarchy. Safety, structural problems and major mechanical issues come first, followed by improvements that can increase rental value and appeal. Cosmetic upgrades come later when the numbers support them.For Bernal, the bigger lesson from a decade in real estate has been discipline. Deals need to be conservatively underwritten, renovation budgets need room for surprises, and projected resale values cannot be treated as guarantees.What began with $500 and a career on the tennis court has evolved into a Connecticut real estate business spanning rentals, student housing, affordable housing and property flips.Images Courtesy: Facebook and istock